Hi!
I thought I would just chime in here

(I have a product called Sweepstakes Ninja which is listed elsewhere on this site that you can look at, which can help make
sweepstaking more fun for you! Link here:
http://www.sweepsadvantage.com/sweepstakes-371408.html)
From what I've seen (personal experience as well as based on a lot of other people), I would pretty much agree with what everyone else has said here so far.
It is pretty much a numbers game, and then there is also an element of luck involved. There is no 'guarantee' that you will win, but if you enter 'consistently', you will greatly increase you chances.
There are 3 main ways of increasing your chances of winning more prizes, more often. They are:
- Enter More Sweepstakes. If you enter 10/day, change it to say 100/day.
- Enter More Often. I.e., if it is a
daily sweepstakes, and you only enter 1/30 days, enter 30/30 days.
- Tell friends and family about the promotions/sponsors/etc. This one might sound a bit interesting, and I'll explain why. Sponsors usually offer sweepstakes because they want to raise their company profile through sweepstakes. I.e., they hope that the money they put in will result in greater sales/more profit. If they offer $1,000 in prizes, they want to hopefully see at least $2,000-$3,000 in return, in terms of goodwill, increased sales, people trying out their product, etc, etc. If you, as well as everyone else, who enters a particular sweepstakes tells friends & family about the promotion, then the company will be most likely to see a 'measurable' return in terms of their sweepstakes. I.e., it was a 'success'. And of course, if they make their money back and then some, most businesses will run even 'more' sweepstakes with 'greater' prizes pools, because the last one was such a success. (I.e., common sense -- i.e., I'd guess that for 99% of people, if you told them to give you a dollar, and you'd give them 3, (and of course they knew it was legit/etc/etc), most would jump at the opportunity). Most businesses pretty much act the same way. So you can help 'increase' the chances of certain types of sweepstakes being held more often & more frequently by telling friends and family about it.
Anyways, hope that helps!
Johnathan